On survivorship bias, hindsight, and why the counterfactual is the only honest way to judge a decision In April 1976, twelve days after co-founding Apple, Ron Wayne sold his 10% stake back to Steve Jobs and Steve Wozniak for $800. You know where this is going. Apple is now worth trillions of dollars, the internet… Continue reading Did It All Work Out?
The Retired Economy
Why a good jobs report makes the market fall — and what that says about a country that has stopped working for a living. A strong jobs report came out, and the market fell. If you’ve spent any time near financial news, you barely register the strangeness of this anymore. More Americans found work than… Continue reading The Retired Economy
We’re Going to Need a Bigger Succession Plan
When you go to buy a business, the conversation is always about the owner. He’s of age. He’s tired. He wants to take some chips off the table and go fishing. That’s the headline risk, and every buyer underwrites it. But the owner isn’t the only one with a foot out the door. Your head… Continue reading We’re Going to Need a Bigger Succession Plan
Paradise Found
Irving Link was in his eighties, sitting in what had long since become his chair, poolside at the Beverly Hills Hotel on a weekday afternoon. He was playing gin rummy in a perfectly fitted tropical-weight suit. He had been playing gin rummy in more or less this spot since 1950. The staff knew his name.… Continue reading Paradise Found
One Envelope
“Then I’m going down the steps, and my wife calls up, ‘Where are you going?’ I say, ‘Well, I’m going to go buy an envelope.’ And she says, ‘You’re not a poor man. Why don’t you buy a thousand envelopes? They’ll deliver them, and you can put them in a closet.’ And I say, ‘Hush.’… Continue reading One Envelope
Show Up
Business travel means airports. Hotels. Conference rooms. It’s a chain restaurant where the conversation doesn’t always click and the dinner sometimes feels like it might never end. And at the end of it, you’re in a hotel room, away from your family, wondering what your kids did today. I’m not telling you this to scare… Continue reading Show Up
Agent-on-Agent
There’s constant debate about who wins the AI race. OpenAI or Anthropic. ChatGPT or Claude or Gemini. OpenClaw or CoWork. The list goes on. Here’s the thing: the winner doesn’t matter. What matters is what happens after the winner is decided, or more precisely, after nobody wins and everybody deploys. Because we’re headed toward a… Continue reading Agent-on-Agent
Brevity over BS
I spent most of my life thinking I was the problem. Everyone around me talks for ten, fifteen minutes. They unspool. They build. They circle back. They restate. They qualify. They add a story. They add another. I say something in one or two. Yes. No. Here’s what I think. Done. I internalized it. I’m… Continue reading Brevity over BS
The Two-Bowl Method
I woke up this morning and went to make eggs. Six of them. A thirty-second job on a normal day—crack, crack, crack, whisk, pan, done. My oldest daughter had other plans. She’s six, and she is eager. Eager to cook, eager to clean, eager to help with anything that remotely resembles a chore. It’s a… Continue reading The Two-Bowl Method
The College Advice I’d Give My Kids
AI is already reshaping which degrees are worth their cost. Companies like Anthropic, which seem to target a new profession for automation every few weeks, are creating real uncertainty around career paths that once felt bulletproof — accounting, law, even software engineering. The question isn’t whether this changes the calculus on college. It’s how. My… Continue reading The College Advice I’d Give My Kids
the counterfactual 